diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index 275265efd50..9396f4e999b 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -314,6 +314,9 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 	private tokenUsageSnapshot?: TokenUsage
 	private tokenUsageSnapshotAt?: number
 
+	// Cloud Sync Tracking
+	private cloudSyncedMessageTimestamps: Set<number> = new Set()
+
 	constructor({
 		provider,
 		apiConfiguration,
@@ -797,6 +800,8 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 				event: TelemetryEventName.TASK_MESSAGE,
 				properties: { taskId: this.taskId, message },
 			})
+			// Track that this message has been synced to cloud
+			this.cloudSyncedMessageTimestamps.add(message.ts)
 		}
 	}
 
@@ -804,6 +809,15 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 		this.clineMessages = newMessages
 		restoreTodoListForTask(this)
 		await this.saveClineMessages()
+
+		// When overwriting messages (e.g., during task resume), repopulate the cloud sync tracking Set
+		// with timestamps from all non-partial messages to prevent re-syncing previously synced messages
+		this.cloudSyncedMessageTimestamps.clear()
+		for (const msg of newMessages) {
+			if (msg.partial !== true) {
+				this.cloudSyncedMessageTimestamps.add(msg.ts)
+			}
+		}
 	}
 
 	private async updateClineMessage(message: ClineMessage) {
@@ -811,13 +825,17 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 		await provider?.postMessageToWebview({ type: "messageUpdated", clineMessage: message })
 		this.emit(RooCodeEventName.Message, { action: "updated", message })
 
+		// Check if we should sync to cloud and haven't already synced this message
 		const shouldCaptureMessage = message.partial !== true && CloudService.isEnabled()
+		const hasNotBeenSynced = !this.cloudSyncedMessageTimestamps.has(message.ts)
 
-		if (shouldCaptureMessage) {
+		if (shouldCaptureMessage && hasNotBeenSynced) {
 			CloudService.instance.captureEvent({
 				event: TelemetryEventName.TASK_MESSAGE,
 				properties: { taskId: this.taskId, message },
 			})
+			// Track that this message has been synced to cloud
+			this.cloudSyncedMessageTimestamps.add(message.ts)
 		}
 	}